


Never Have I Ever

by frozen_delight



Category: Supernatural
Genre: Angst, Brotherly Banter, Episode: s11e09 O Brother Where Art Thou, First Time, M/M, Schmoop, Season/Series 11
Language: English
Status: Completed
Published: 2015-12-11
Updated: 2015-12-11
Packaged: 2018-05-06 05:40:14
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,683
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5405108
Author URL: https://archiveofourown.org/users/frozen_delight/pseuds/frozen_delight
Summary: <blockquote class="userstuff">
              <p>The night before Sam goes to talk to Lucifer, the boys get drunk together.<br/>The obligatory drinking games lead to Wincest cliché fic, and a not quite so obligatory missing scene for 11x09 “O Brother Where Art Thou?”.</p>
            </blockquote>





	Never Have I Ever

**Author's Note:**

  * For [MisplacedLonelyHeartsAd](https://archiveofourown.org/users/MisplacedLonelyHeartsAd/gifts).



> Unbetaed, apologies for any mistakes.
> 
> For my wincesty partner in crime MisplacedLonelyHeartsAd, who shares my passion for the blanket in the backseat.

Dean was the one who’d started it.

They were doing the only sensible thing you could on a night like this—sitting next to each other on his bed, chugging beers. At some point they’d stripped down to their t-shirts and boxers. They didn’t talk much. What was there to say? _This is a horrible idea? I’m scared?_

“Hey, at least Rowena’ll be pleased to see you again.” Dean knocked his shoulder against Sam’s with a lewd grin. “She looked mighty thrilled the last time you slapped those cuffs on her wrists.”

“Dude.” Dean watched the tectonics of Sam’s face rearrange themselves into a glacial landscape of contempt.

“Come on, Sammy, admit it. She has a little thing for you.”

“I think she has a little thing for Cas.”                

Dean nearly choked on his beer. “Cas? Seriously? Man, she’s so gonna eat him alive.—Guess we’ll have to tell him to keep the chains on at all times.” He whistled and raised his bottle towards his brother in mock salute before taking a long gulp. “Never have I ever participated in bondage, not that I’m judging.”

He noticed then that Sam was gazing down at his own bottle with a wistful little smile, private enough that it made part of Dean want to run for the hills and never look back. Moments like this reminded Dean that Sam had a history independent of his own, had _depth_. While all the depth Dean could call his own was inside the steep neck of his beer bottle.

He shook himself, focused on the obvious. “You mean, you—” He couldn’t help but be horrified. And impressed. This was his little brother after all.

Sam was still smiling down at his bottle. “Sometimes, Jess wanted to try something…”

“You never told me that!”

“Of course I never told you that! It’s not like we sit down every Sunday for dinner and discuss my sex life with my dead girlfriend.”

“Yeah, that would be—ugh.—It’s just, this stuff, and you, it’s… _weird_. Good weird,” Dean hastened to add.

“Yeah.” Sam’s smile turned playful, challenging even. He raised his bottle. “Talking about _good weird_. Never have I ever worn my girlfriend’s underwear.”

“How do you even—?” Dean closed his mouth and took a large gulp from his beer.

Sam leaned closer, his expression a mixture of confidential and teasing. “I’ve been watching you all my life, Dean.”

“Whoa, that sounds kinda creepy in this context.”

“Guess so,” Sam acknowledged, perfectly unfazed.

Dean glared at him, fighting a smile. Sam was just trying to mess with him. Oh, this was so on!

“Never have I ever—wait for it—” he lifted his right index finger “—never have I ever been afraid of clowns.”

Sam snorted and rolled his eyes, but took the obligatory sip from his beer.

After that, the game quickly escalated. Thing was, they already knew most of each other’s embarrassing secrets, and there were very few things in life they hadn’t both done at some point. There were very few things they hadn’t done, full stop. _Never_ wasn’t really a word in the Winchester vocabulary. So instead they simply grabbed the opportunity to rib each other, to hell with the rules. The only win available was to forget what lay ahead just for a minute or two, and both of them eagerly grasped at it as a drowning man would a lifeline.

“Never have I ever ducked my chores,” Dean accused Sam, only to have Sam retaliate, “Never have I ever chucked research to watch Downton Abbey.”

“Hey, it was an accident!” Dean protested. “Never have I ever left a tissue in the pocket of my jeans before putting them in the washer.”

“Never have I ever been an obsessive-compulsive pocket-checker.”

“Never have I ever been an obnoxious little brother.”

He expected Sam to respond with something like _Never have I ever been an overbearing older brother._ Instead, Sam slid closer towards him, his expression shifting from openly amused to thoughtful.

“Never have I ever looked up to anyone more.”

The words were quiet. This was what Sam sounded like when he prayed.

Involuntarily, Dean shivered and put down his beer on the nightstand with a clunk. There was no doubt in Sam’s eyes. No fear either. Just calm. And something Dean couldn’t quite read. Something like tenderness.

“Sammy…”

He felt lost. Threatened. He could shoot crap, crack jokes and get drunk like a pro—but last words? There was no way of telling his little brother _You’re my all the world_ that wouldn’t sound like fumbling around in a foreign tongue. There was no way of wrapping up every single apology he owed Sam with a nice bow and all. Not even to mention there was no way of guaranteeing his apologies wouldn’t turn into accusations while he was at it. ’Cause bursting out with something like _You know that time you jumped into a hole in the ground and made me watch and forbade me to follow you? That was the worst thing you ever did to me!_ would really set the mood for their big enterprise the next day.

Slowly, Sam reached out and cupped the side of Dean’s face, as if to say _Don’t be afraid_. Dean could feel Sam’s fingers spread over his cheek, long, warm, and strong; fingers which had crushed demon’s necks and caressed their skin; fingers which had rescued drowning children from deadly waters and comforted grieving families. Fingers which had marked up Dean’s skin in every symbol of love, anger, bitterness, grief and forgiveness known to man. Fingers which had reached out to Dean as long as he could remember.

Carefully, Dean placed his hand on top of Sam’s.

“Never have I ever loved anyone more,” Sam told him, still in that confessional tone.

Dean swallowed nervously at the sound of the infamous four-letter word.

And suddenly Sam’s other hand was on his face too, and Sam’s face was only inches from his, and Sam’s eyes were searing him with their intensity. “Never have I ever—” Sam’s gaze flickered down to his mouth “—wanted to kiss anyone—” Sam pressed their lips together, a fleeting dry touch of affection, and drew back again “—more.”

As if in a trance, Dean touched a finger to his lips. Stared at Sam, took in the earnest fire of his expression, somehow managing to look simultaneously crushed and hopeful.

He remembered Piper, a bright blonde dream in the middle of Sam’s bleak visions, remembered Sam buoyantly rebuttoning his shirt in the seat next to him, remembered the blanket in the backseat that Sam hadn’t bothered to fold up afterwards. At the time he’d thought Sam had left it lying there as proof he hadn’t soiled the interior of Dean’s freshly cleaned car, knowing full well Dean would have made him walk the rest of the way if he had. But what if it had been an invitation, even back then?

_You don’t ever want something more? You don’t ever think about something? Not marriage or whatever. But…something? You know, with a hunter? Somebody who understands the life?_

He wasn’t nearly drunk enough to make such a potentially disastrous decision. But when your brother kisses you on the night before said brother is going to meet up with Satan and his darkest nightmares in the most horrific parts of Hell, you don’t hesitate over a technicality—of course you kiss him back.

So Dean did.

Sam’s mouth readily opened under his. The first swipes of his tongue were tentative, then grew steadily more insistent, tasting every unspoken word in the unholy cavity of Dean’s mouth. One of his hands had moved to Dean’s neck, keeping him in place, while the other roamed over the small of his back, slipping under his t-shirt, dipping below the waistband of his boxers, bold and sure.

Dean gripped Sam’s strong forearms tight enough to bruise, knowing Sam could take it, and let himself get drunk on the motions of Sam’s hands on him, Sam’s tongue inside him, more intoxicating than beer had been for him in years. He’d been kissed more times than he could count, but never like this—like every single fiber inside him was being dragged to confession, and instead of fighting it every step of the way, Dean abandoned himself to the sensation. Caressing every inch of Sam’s lips with his mouth, tongue and teeth, he soaked up a taste of purification, of salvation, and of everything else Sam could give him.

When they broke apart, he was lying on his back, t-shirt ridden up, with Sam kneeling beside his hipbone, staring down at him with wide, dazed eyes.

Dean took in his brother’s flushed cheeks and grinned. For the first time since Amara had laid her hands on his face the itch her touch had left beneath his skin had disappeared. All that thrummed there now was want and desire, all directed at the person next to him.

He pulled up one of his legs and let it fall to the side in an open invitation.

Sam took the hint and crawled between Dean’s legs, but instead of getting down to business—and Dean really hoped his nerdy little brother knew exactly what that meant in this case, because he’d never cared much about researching the logistics of gay sex himself—he captured Dean’s ankle in one of his hands and began to nose and kiss his way up Dean’s leg. He nuzzled the back of Dean’s knee, bit down on the inside of his thigh, pressed open-mouthed kisses to the hollow of his hips. Then his mouth and hands moved further up, ignoring Dean’s straining erection, lingering on every spot where Dean couldn’t suppress a shudder, a moan, a curse or a sigh. By the time Sam’s mouth reconnected with his, Dean had been reduced to a quivering mess.

“Please, Sammy,” he whispered urgently against his brother’s lips, and exhaled in relief when one of Sam’s big, strong hands finally snuck beneath his waistband and wrapped itself around his already leaking cock.

Under the skilled pressure of Sam’s hand, with Sam’s muscular thighs bracketing his, and the thought of Lucifer rattling around the back of his head like a non-exorcible poltergeist, it didn’t take him long to come, burying a moan in Sam’s sweaty neck.

He let Sam maneuver his heavy, blissed-out limbs until he was lying on his side with Sam behind him; barely even noticed Sam tugging down his soiled boxers and removing his own, until there was suddenly a hot, hard pressure between his thighs.

“Legs together,” Sam told him in a voice that booked no refusal and damn if Dean’s stupid heart didn’t stutter at the tone. Who’d have thought bossy little brothers could be such a turn-on?

“So it really does make you all tingly inside,” Sam murmured against a spot just below his ear as his cock slid between the flesh of Dean’s thighs.

“No idea what you’re talking about,” Dean grumbled and bit off a groan when Sam started to rut against him.

“You said so once, don’t you—” Sam stilled behind him with a gasp. “No, of course you wouldn’t remember.”

The anguish in his brother’s words told Dean all he needed to know. Sam was talking about Broward County, that awful black spot in both their memories, though for very different reasons.

He clasped the hand Sam had slung over his waist and threaded their fingers together.

“It’s okay, Sammy. I get it. But I’m still here.” He gulped. “And it goes both ways, you know.”

When the only reply he received was Sam’s low breathing against his neck, he continued with greater urgency, squeezing Sam’s hand, “I can’t do this without you, man. I—I killed Death so you could live. I let out the Darkness into the world so we could be together. That was the point, you and me. Don’t—don’t you forget that.”

“I won’t,” Sam said softly, a line of heat and muscle against Dean’s back.

“Sam.” The word was out of his mouth before he even realized it. That was why he hated chick-flick moments so much—you open those floodgates and then everything just streams out of you with no way to stop it. “If things go south tomorrow—don’t try to—just get out. Please!”

He remembered asking the same thing of Dad, before he’d set off to hand over the fake Colt to Meg. He felt Sam’s intake of breath against his shoulder, could sense that he too recalled the scene and how it had felt like the end of the world back then; back when they’d been too young and stupid to know better.

“Okay.”

Dean closed his eyes, let those two syllables wash over his skin and calm his anxious heart. Then he said, “Well, what are you waiting for, cowboy? Get off or…get off.”

Behind him, Sam chuckled. “Seriously, Dean, I think this is the worst line you’ve ever come up with, and that’s saying something.”

“You love it.”

“I do,” Sam concurred, and finally began to move again.

Frenzied grunts and the rhythmic slap of skin on skin swallowed up any remaining gloom, and soon Sam came, spurting over Dean’s balls and ass with a ragged groan.

As Sam sagged against him, Dean took the opportunity to flip them until Sam was lying on his back and Dean on top of him, because there was no way _he_ was sleeping in the wet spot tonight.

He felt Sam’s come dribble down his thigh. They were going to be disgusting tomorrow. And the sheets. And their clothes.

Dean spread himself across Sam’s chest, Sam’s steady heartbeat against his cheek, and found he didn’t care overly much.

“Um…Dean? Are you… _cuddling_ me?”

“’S my bed,” Dean grumbled against Sam’s chest.

He could hear the amusement in Sam’s voice. “You want me to leave?”

He wrapped himself more tightly around Sam’s torso. “Shut up and go to sleep!”

Just when Dean was ready to drift off, Sam spoke again. “Promise me you won’t freak out tomorrow?”

Affronted, Dean pinched Sam’s chest. “I never freak out!”

Sam trapped Dean’s hand in his and dropped a kiss to the crown of his head. “Promise me anyway?” He sounded soft, fond, open. Like the little boy who’d believed that a single _It’s okay_ from Dean’s lips could make it so.

Dean let out a theatrical sigh and wriggled his hand out of Sam’s grip. “Alright, I promise, now can we finally go to sleep?”

After a beat, Sam said, “Thanks, Dean.”

Then silence fell again.

Against his auricle, Sam’s heart thumped like the hollow, portentous gong of an old church bell in an abandoned graveyard. Dean found himself counting each beat, every single one heralding that all too soon this night too would be over.

“You know what sucks?” he eventually asked into the dark, unable to regain the state of sleepy tranquility he’d been in before. He could tell from Sam’s breathing that he wasn’t asleep either. The words came out choked, and he drew in a wet breath. “You never gave me the chance to say _We’ve got tonight, who needs tomorrow_.”

Sam laughed. It sounded close to a sob. “That’s a real tragedy.” His arms contracted around Dean like a vow. “But you know, we’ve still got tomorrow and every single day after that.”

“’Course we do,” Dean agreed with all the conviction he could put into his voice, rubbing his cheek against Sam’s pecs and settling more comfortably in the cocoon of Sam’s arms. Rowena might screw them over. Crowley might screw them over. Lucifer might screw them over. Hell, probably all three _would_ screw them over. But this was too important not to build on faith for once. And Dean might not share Sam’s faith in God, a higher justice, a divine plan and all that crap, but he could do his best to put his faith in Sam instead. “Now go to sleep, you giant sap.”

**Author's Note:**

> Thanks for reading. Feedback is love.
> 
> You can also talk to me here: [LJ](http://frozen-delight.livejournal.com/) | [Tumblr](http://frozen-delight-blog.tumblr.com/)


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